9-Day Italy Self-Drive Road Trip With Itinerary from Rimini traveling west to Bologna, Florence, Siena, and Arezzo

Experience an unparalleled adventure on day 2 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Bologna. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Bologna. You will spend 1 night here for some well-deserved relaxation.

Today, you'll explore some of the most beautiful places in Rimini, including a public square, a monument, a church, a palace and much more! Start your day with a visit to Piazza Santo Stefano. This worthwhile public square is a must-visit in the city. When you’re ready for your next discovery, continue to Two Towers, which may be one of the most picture-perfect places you will experience today.

One of the best things about exploring Rimini on a self-guided tour is that you set the pace. There’s plenty of time for detours and discovering hidden gems. When you’re ready for your next stop, make your way to Bologna Cathedral, an up-and-coming church in the city. If you’re up for more discoveries, don’t forget to reserve some time for Palazzo Re Enzo and Fountain Of Neptune, Bologna. End your day with a visit to Piazza Maggiore, a famous public square that’s sure to leave a lasting impression.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Bologna. Bologna offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Bologna. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Treat yourself to a delicious dinner at Ristorante Ciacco, an excellent option for tonight's dining. Looking for something different? Ristorante Ballarini offers a tantalizing alternative with its diverse menu. And don’t miss Sfoglia Rina. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Bologna.

Continue your lively evening at Bar Al Bricco D'oro, a perfect place for winding down or revving up the night, depending on which mood you’re in. Bar Freud E Squisito is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Osteria Del Sole ensures a night out tailored to your taste.

Celebrate another amazing day of your road trip adventure in Italy!

Dive into day 3 of your remarkable road trip in Italy. Today you will explore Florence, where you will have the opportunity to experience all the top things to see and do. At the end of the day, you’ll unwind at one of the finest accommodations in Florence. You’ll stay here for 2 nights.

Today’s agenda in Bologna includes a food market, a church, a historical landmark, an art gallery, a public square and much more! Central Market is must-visit food market and a great starting point for the day. Next, continue your journey to Cathedral Of Santa Maria Del Fiore, an astonishing church, located just a leisurely stroll away. Next, head to Florence Baptistery, a history-steeped church, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Bologna. When you're ready, let your sightseeing route take you to the wondrous Ponte Vecchio. If you’re looking for more, Uffizi Gallery is also a widely recognized attraction that is worthwhile a visit. Lastly, don’t miss Piazza Della Signoria, a place of enchanting interest in the city.

When you’re done exploring for the day, you’ll drive to your hotel in Florence. Check in and spend some time relaxing before you head out to tour the city.

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Florence. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Make sure to reserve a table at Ristorante Oliviero 1962, an iconic dining spot in Florence. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Di Poneta Novoli, a popular restaurant in Florence. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Caffe San Firenze, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Extend your evening after a delightful meal by visiting Manifattura, which offers the perfect atmosphere for a night out. Moreover, Se·sto On Arno Rooftop Bar is another popular option for a drink or two. Likewise, Il Vinile also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

Head back to your accommodation in Florence and get some rest in preparation for another magical day of your road trip in Italy!

At the end of the day, you'll drive back to Florence, where you'll stay for 1 night more.

Oltrarno is a fantastic place you can explore today in Pisa. This neighborhood is a testament to the city’s character, and it's easy to spend hours just walking around and admiring the surroundings. Soak in the Pisa-way-of-life and visit all the nearby sights.

Florence is brimming with adventures. Today’s wonderful stops include a public square, a monument, a church, an observation deck and much more! Begin your sightseeing adventure at the iconic Piazza Del Duomo, Pisa and allow yourself time to explore. Just a short distance away you'll find your next stop, Leaning Tower Of Pisa, a detailed monument that draws visitors from far and near.

Continue your journey to Basilica Of Santa Croce In Florence, one of the city’s most interesting spots that you shouldn’t miss. Another great site to visit is the famous Piazzale Michelangelo.

When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Florence.

As dinnertime approaches, it's time to head out for a bite to eat in Florence. If you are looking to dine at a popular restaurant in the city, it's often a good idea to reserve a table in advance.

Treat yourself to a delightful dinner at Ditta Artigianale, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Trattoria Da Burde? It's another excellent option with a diverse menu. Consider reserving a table at Casa Toscana as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Florence.

Keep the evening going at Bar 50 Rosso, a great choice for enjoying the after-dinner hours with a drink. You could also go to Bitter Bar, which offers a similarly pleasant setting and great drinks. Another option is Archea Brewery, which provides an inviting environment for unwinding after a busy day out.

Celebrate another amazing day of your road trip adventure in Italy!

On day 5 of your road trip in Italy, you will get a true taste of the freedom a self-drive vacation in Europe entails. Today’s travel plans include stops at the most scenic, wondrous, and interesting places in Siena. In the evening, you’ll end up in Siena, where you will stay for 2 nights.

Get ready for a day filled with fun adventures, scenic views, and picturesque spots in the charming city of Florence. Your adventure starts at Basilica Of San Domenico, a beloved local hot spot. Another notable attraction to explore is Piazza Del Duomo. This underrated public square is known for its grand appeal.

After soaking in the highlights of these sights, take some time to wander Florence's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Siena Cathedral. This history-steeped church offers a fascinating experience that many visitors find memorable. Pubblico Palace is also worth visiting, along with Piazza Del Campo. These standout landmarks offer unique experiences that add to the day’s enjoyment. End your day at Tower Of Mangia. This worthwhile monument provides a fitting finale to your sightseeing.

At the end of the day, you will drive to Siena, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

As dinnertime approaches, it's time to head out for a bite to eat in Siena. If you are looking to dine at a popular restaurant in the city, it's often a good idea to reserve a table in advance.

Have a fantastic dining experience at Enoteca I Terzi, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Ristorante Tar-Tufo offers an enticing alternative with its varied menu. Additionally, Antica Trattoria Papei is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Siena.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Meet Life Cafè, known for its inviting atmosphere. Maudit Pub is another great option if you’re looking for a place to get the night started. Similarly, Bar Impero Siena provides a great setting to enjoy the night away.

Relax and reminisce about your day in Italy and look forward to more memorable moments to come!

On day 6 of your road trip, you’ll start and end your day in Siena, where you'll stay for 1 night more.

Enjoy the perfect balance of relaxation and exploration in Siena today. One of the most often recommended attractions included on the itinerary is Porta San Giovanni. This historic monument will help you start your sightseeing on top. Then, take a leisurely stroll to Piazza Del Duomo and learn what makes this UNESCO world heritage-listed public square unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the up-and-coming Rocca Di Montestaffoli. After exploring the castle, head to Parco Della Rocca. This intriguing park is a highlight in Siena. As your day continues, stop by Chiesa Di Sant'agostino, known for its photogenic features. Lastly, don’t forget to check out the often recommended Fortezza Medicea (siena). Enjoy exploring this incredible monument at your own pace.

When you’re done exploring for the day, you’ll return to Siena and your accommodation.

As you explore more of Siena, you'll discover that its culinary landscape is as diverse as its attractions. Whether you're craving traditional dishes bursting with local flavors or innovative creations that push the boundaries of taste, you're sure to find a dining experience that satisfies your cravings.

Enjoy a lovely dining experience at Osteria Quattro Venti, a popular restaurant in Siena. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Siena at Fischi per Fiaschi, another great place to eat. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. A third option to check out is the top-rated Osteria da Divo. It’s yet another ideal choice to enhance your time in Siena tonight.

Keep the excitement of the evening going by visiting a bar or two. Charlie Mixology Bar Di Aldinucci Riccardo is an excellent place to start. You could also check out Bar Pinacoteca, offering a different kind of charm. A last recommendation for the day is San Paolo Pub. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

Savor another day of unforgettable experiences in Italy!

Embark on another extraordinary experience on day 7 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Arezzo. At the end of the day, you will enjoy the comforts of a top-rated hotel in Arezzo, which will be your home away from home for 1 night.

Today’s well-planned self-sightseeing route offers several family-friendly attractions, photo-friendly spots, and history-rich sites. Whether you decide to explore Siena on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Casa Vasari is the first of them. Spend some time admiring this photogenic museum before continuing your journey. The Medici Fortress Park is your next stop. This increasingly popular park is one of the best-rated sights in Siena.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Piazza Grande. This enchanting public square is a sight to behold. To round off your sightseeing experience, visit Santa Maria Della Pieve and San Francesco, Arezzo.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Arezzo. Arezzo offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

As you explore more of Arezzo, you'll discover that its culinary landscape is as diverse as its attractions. Whether you're craving traditional dishes bursting with local flavors or innovative creations that push the boundaries of taste, you're sure to find a dining experience that satisfies your cravings.

Don’t miss out on dining at Il Covo dei Briganti, a top-rated dining destination in Arezzo. If you're in the mood to try something new, consider La Clandestina, another top spot with a mouthwatering menu. You might also want to secure a reservation at Ristorante Logge Vasari. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Arezzo this evening.

Continue your evening by exploring the vibrant nightlife scene at Liquid Bar, a prime destination for a thrilling night out.

As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in in Italy.

On day 8 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Urbino. When you’re not sightseeing, take time to relax at your selected hotel in Rimini, where you’ll be staying for 1 night.

Prepare for a day full of fun adventures, scenic views, and picturesque spots. When you’re ready, kick off your sightseeing adventure at Palazzo Ducale. This well-known palace is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Galleria Nazionale Delle Marche, one of the town’s best highlights.

Next, check out Oratory Of St John The Baptist, Urbino, one of the most worthwhile places to see in Arezzo. This church is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Casa Santi. Wander around and soak in the photogenic atmosphere this museum offers. Then, head to Fortezza Albornoz, a top-rated castle that adds another dimension to your day.

When you’re done exploring for the day, you’ll drive to your hotel in Rimini. Check in and spend some time relaxing before you head out to tour the city.

Indulge in a memorable dining experience at one of Rimini's most popular restaurants, and connect with friendly locals for an authentic adventure.

Dine in style at Osteria Brodo di Giuggiole, a top recommendation for dinner tonight. Or, for a change of pace, Hotel Touring boasts a menu that's sure to impress. Also, be sure to check out Ristorante Lo Zodiaco Rimini. Known as a local hotspot, it’s a great choice for tonight in Rimini.

After your meal, keep the night alive at a bar like Hobo's, known for its lively atmosphere. Sunflower City Backpacker is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Bar Capogiro offers an excellent atmosphere for those looking to amp up the evening.

Say good night to Rimini and look forward to another great day of your road trip in Italy!